Chemistry > QUESTIONS & ANSWERS > CHEM 30 Fall 2014 Final Review 2 Solution s • Harvar d Univer sity • CHEM 30 (All)
CHEM 30 Fall 2014 Final Review 2 Solution s • Harvar d Univer sity • CHEM 30
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Chemistry 30 Weekly Review 2 September 19, 2014 1. (a) Lactone 2 is significantly more susceptible to nucleophilic attack at the carbonyl than acyclic ester 1. Explain. O O Me O Me 1 2 Both est... ers have the n -> *CO interaction. However, acyclic ester 1 has an additional nsp2 -> *CO interaction which is lacking in 2. This additional interaction stabilizes 1. Ester 1 Lactone 2 Et Et O O O O Et Et nO *CO nO *CO nO *CO no overlap of (p) (sp2) (p) sp2 O lone pair into *CO (b) Explain the observed bond angles in the lactone below = 6.9 Orbital overlab between a lone pair orbital on the carbonyl oxygen and the *CO shown below is improved by the observed bending of the carbonyl group [Show More]
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